TWI363760B - Novel condensed polycyclic aromatic compound, production method thereof, and usage thereof - Google Patents
Novel condensed polycyclic aromatic compound, production method thereof, and usage thereof Download PDFInfo
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- TWI363760B TWI363760B TW096139747A TW96139747A TWI363760B TW I363760 B TWI363760 B TW I363760B TW 096139747 A TW096139747 A TW 096139747A TW 96139747 A TW96139747 A TW 96139747A TW I363760 B TWI363760 B TW I363760B
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- -1 polycyclic aromatic compound Chemical class 0.000 title claims description 58
- 238000004519 manufacturing process Methods 0.000 title claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 160
- 239000004065 semiconductor Substances 0.000 claims description 152
- 239000000463 material Substances 0.000 claims description 114
- 238000000034 method Methods 0.000 claims description 76
- 239000000126 substance Substances 0.000 claims description 43
- 230000005669 field effect Effects 0.000 claims description 38
- 239000010409 thin film Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 150000001787 chalcogens Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000000524 functional group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
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- 239000000203 mixture Substances 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 8
- WQOXQRCZOLPYPM-UHFFFAOYSA-N Dimethyl disulfide Natural products CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 5
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
- C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/30—Organic light-emitting transistors
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Thin Film Transistor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006290192 | 2006-10-25 |
Publications (2)
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| TW200838866A TW200838866A (en) | 2008-10-01 |
| TWI363760B true TWI363760B (en) | 2012-05-11 |
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|---|---|---|---|
| TW096139747A TWI363760B (en) | 2006-10-25 | 2007-10-23 | Novel condensed polycyclic aromatic compound, production method thereof, and usage thereof |
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| US (1) | US8232546B2 (ko) |
| EP (1) | EP2098527B1 (ko) |
| JP (1) | JP4958119B2 (ko) |
| KR (1) | KR101177970B1 (ko) |
| CN (1) | CN101528753B (ko) |
| TW (1) | TWI363760B (ko) |
| WO (1) | WO2008050726A1 (ko) |
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| JP5288372B2 (ja) * | 2008-06-19 | 2013-09-11 | 国立大学法人広島大学 | 芳香族化合物の誘導体とそれらの中間体の製造方法 |
| JP2010083785A (ja) * | 2008-09-30 | 2010-04-15 | Chisso Corp | 平面性の高い分子構造を有する化合物およびこれを用いた有機トランジスタ |
| US7872258B2 (en) * | 2008-11-19 | 2011-01-18 | Xerox Corporation | Organic thin-film transistors |
| EP2402348B1 (en) * | 2009-02-27 | 2017-04-12 | Nippon Kayaku Kabushiki Kaisha | Field effect transistor |
| JP5467676B2 (ja) * | 2009-05-26 | 2014-04-09 | 日本化薬株式会社 | 芳香族化合物の製造方法 |
| JP5390959B2 (ja) * | 2009-06-30 | 2014-01-15 | ウシオケミックス株式会社 | スルホン構造を有する有機半導体化合物 |
| KR101068575B1 (ko) * | 2009-07-03 | 2011-09-30 | 주식회사 하이닉스반도체 | 반도체 장치 및 그 제조방법 |
| JP2011162510A (ja) * | 2010-02-12 | 2011-08-25 | Teijin Ltd | 新規なα−ジケトン化合物、及び有機半導体デバイス |
| KR101604513B1 (ko) * | 2009-08-28 | 2016-03-17 | 데이진 가부시키가이샤 | 신규한 부가 화합물, 축합 다고리 방향족 화합물의 정제 및 제조 방법, 유기 반도체막 형성용 용액, 및 신규한 α-디케톤 화합물 |
| JP2011148743A (ja) * | 2010-01-22 | 2011-08-04 | Teijin Ltd | 縮合多環芳香族化合物の精製及び製造方法 |
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| JP5733553B2 (ja) * | 2010-01-12 | 2015-06-10 | 株式会社リコー | 置換基脱離化合物および有機半導体材料およびその膜およびそれを用いた有機トランジスタ |
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| WO2020045597A1 (ja) * | 2018-08-31 | 2020-03-05 | 国立大学法人 東京大学 | カルコゲン含有有機化合物、有機半導体材料、有機半導体膜、及び有機電界効果トランジスタ |
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| JP4177286B2 (ja) * | 2004-05-11 | 2008-11-05 | 独立行政法人科学技術振興機構 | 新規なアントラセン誘導体 |
| JP2006031893A (ja) | 2004-07-21 | 2006-02-02 | Matsushita Electric Ind Co Ltd | 光ディスク装置 |
| JP2006077888A (ja) | 2004-09-09 | 2006-03-23 | Nsk Warner Kk | クラッチハブ |
| CN101111497B (zh) | 2004-09-14 | 2013-10-30 | 康宁股份有限公司 | 稠合噻吩及其制备方法和用途 |
| JP2006199909A (ja) | 2004-12-20 | 2006-08-03 | Seiko Epson Corp | 導電性材料用組成物、導電性材料、導電層、電子デバイスおよび電子機器 |
| WO2006077888A1 (ja) * | 2005-01-19 | 2006-07-27 | National University Of Corporation Hiroshima University | 新規な縮合多環芳香族化合物およびその利用 |
| JP5499422B2 (ja) * | 2006-06-28 | 2014-05-21 | コニカミノルタ株式会社 | 有機半導体材料、有機半導体膜、有機薄膜トランジスタ及び有機薄膜トランジスタの製造方法 |
| KR20080100982A (ko) * | 2007-05-15 | 2008-11-21 | 삼성전자주식회사 | 헤테로아센 화합물, 이를 포함하는 유기 박막 및 상기박막을 포함하는 전자 소자 |
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- 2007-10-22 KR KR1020097010362A patent/KR101177970B1/ko active IP Right Grant
- 2007-10-22 US US12/312,083 patent/US8232546B2/en active Active
- 2007-10-22 JP JP2008540982A patent/JP4958119B2/ja active Active
- 2007-10-22 EP EP07830303.9A patent/EP2098527B1/en active Active
- 2007-10-22 WO PCT/JP2007/070569 patent/WO2008050726A1/ja active Search and Examination
- 2007-10-22 CN CN200780039700XA patent/CN101528753B/zh active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2098527B1 (en) | 2016-03-30 |
| KR20090074248A (ko) | 2009-07-06 |
| JP4958119B2 (ja) | 2012-06-20 |
| KR101177970B1 (ko) | 2012-08-28 |
| CN101528753B (zh) | 2012-05-23 |
| US8232546B2 (en) | 2012-07-31 |
| TW200838866A (en) | 2008-10-01 |
| EP2098527A4 (en) | 2012-05-23 |
| EP2098527A1 (en) | 2009-09-09 |
| US20100065826A1 (en) | 2010-03-18 |
| WO2008050726A1 (fr) | 2008-05-02 |
| CN101528753A (zh) | 2009-09-09 |
| JPWO2008050726A1 (ja) | 2010-02-25 |
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